330636-99-2

Upstream product

• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 479692-19-8 methyl N-(N-cinnamoyl-(L)-prolyl)-3-phenylaziridine-2-carboxylic acid 
• 475640-21-2 (2S,3R)-3-Phenyl-1-{(S)-1-[(E)-(3-phenyl-acryloyl)]-pyrrolidine-2-carbonyl}-aziridine-2-carboxylic acid ethyl ester 
• 107173-65-9 N-(3-phenylpropenoyl)-L-proline 
• 84024-60-2 trans-3-phenylaziridine-2-carboxylic acid ethyl ester 

Downstream Products

• 330637-00-8 (S)-4-Methyl-2-[(Z)-3-phenyl-2-({(S)-1-[(E)-(3-phenyl-acryloyl)]-pyrrolidine-2-carbonyl}-amino)-acryloylamino]-pentanoic acid methyl ester 

Relevant academic research and scientific papers

Reverse turn induced π-facial selectivity during polyaniline-supported cobalt(II) salen catalyzed aerobic epoxidation of N-cinnamoyl L-proline derived peptides

A novel chemo- and diastereoselective aerobic epoxidation of the N-cinnamoyl peptides catalyzed by polyaniline-supported cobalt(II) salen (PASCOS) is described. The N-cinnamoyl proline derived peptides 1 show a high π-facial selectivity during these epoxidations. The origin of this diastereoselectivity in I has been attributed to (i) the propensity of the N-cinnamoyl proline amide to exist predominantly as trans rotamer in CDCl3, DMSO-d6, and CH3CN medium and (ii) existence of these peptides as organized structures (γ- and β-turns) due to the presence of intramolecular hydrogen bonds. An extensive solution NMR and MD simulation study on 1d and 1f indicates that the origin of the high π-facial selectivity is due to the well-defined γ- and β-turns which result in the hindrance of one face of the cinnamoyl double bond in the transition state of the epoxidation reaction.

Synthesis and conformation of proline containing tripeptides constrained with phenylalanine-like aziridine and dehydrophenylalanine residues

Tripeptides containing proline and analogues of phenylalanine lead to the formation of β-turn structures. The synthesis and β-turn properties of four such compounds are discussed.